The story could scarcely be more simple: two committed patriots off to find America. The iconic, oft-referenced sequence in 1969’s psychedelic biker opera Easy Rider features the film’s twinned anti-heroes, Billy and Wyatt, tearing down a sprawling U.S. highway astride two choppers at some impossible speed, soundtracked by one of the greatest badass statements of purpose rock’n’roll ever yielded: Steppenwolf’s “Born to Be Wild.” It’s a song that perfectly bisects the dueling hippie impulses between the communitarian and utopian, and the hedonistically self-fascinated, a painful cleavage which was coming to the fore just as Easy Rider hit screens in July 1969.

Can you picture it? Set against the monster rock riffs of lead guitarist Michael Monarch, singer John Kay’s edict to “take the world in a love embrace” sits nervously alongside the tune’s insinuating thirst for danger: “I like smoke and lightning/Heavy metal thunder.” This is the dichotomy that would define both the film and the soundtrack, the pastoral, pacific drop-out resistance of the Summer of Love running directly into the fraught entropy of an ersatz movement losing steam and beginning to cannibalize itself. It’s an image of such pure lawless liberation, from blue-to-red-state America, I’m not sure we’ve ever fully recovered. It’s way more “don’t tread on me” than “come on people now, smile on your brother.” In my mind—and I’ve seen the movie many, many times—I always think this is how Easy Rider starts.

The actual first scene in Easy Rider is intensely uneasy, a tenuous south-of-the-border drug deal that has all the hallmarks of a classic Treasure of the Sierra Madre-style misunderstanding. But no. Peter Fonda and Dennis Hopper—the film’s titular motorcycle muses—manage to fence what looks like a bumper crop of coke to a louche-looking drug connect played by Phil Spector, who sends them off with generational cash in exchange. So, the first song you hear in the movie is not Steppenwolf’s epochal nature-call, but rather their cover version of Hoyt Axton’s sad and cynical “The Pusher.” Soon enough, our heroes are unleashed, furious and stoned, on the now-decommissioned highways of 1969. But they’d never outrun the slow creeping blues of the first Steppenwolf song, even as Hopper’s Billy and Fonda’s Wyatt lit out to what was ostensibly their last deal gone down. Some sage once opined, “To live outside the law you must be honest.” Wyatt and Billy are never honest with themselves until it’s too late. The drugs got harder, the compromises more equivocal. The equation changed. After the wild success of Easy Rider, Hopper bragged that it was the single biggest factor in getting cocaine into the everyday vernacular of American drug abuse. He boasted, “The cocaine problem in America is really because of me. There was no cocaine before Easy Rider on the street. After Easy Rider, it was everywhere.”

The extent to which Easy Rider was a borderline impossible film to make necessitates a wild litany of New Hollywood lore involving everyone from the producers Bob Rafelson and Bert Schneider to the principals given a shoestring budget and charged with delivering a motorcycle picture, originally, and unpromisingly, called The Loners. The script, to the extent it existed, was a largely improvised collaboration between Hopper, Fonda, and the great Terry Southern, recently of Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb. Filming was challenging. Hopper, directing for the first time, was a paranoid and psychotic bully with a resolute vision, constantly undermined by chemically induced megalomania. The cast and crew were so convinced of his capability for violence that few dared to intervene on his impulses. Test-filming in New Orleans with an inexperienced skeleton team yielded more questions than answers. Hopper’s first edit was four and a half hours. The studio proposed sending him on vacation, which for some reason he agreed to. When he got back from Taos, the movie was 94 minutes and obviously improved. Hopper rioted, threatening everyone, before giving up and admitting the new cut was superior. Nobody was murdered in the making of the film, except perhaps the enduring vestiges of the old studio system. In the ensuing months, Easy Rider earned a shocking $41.7 million domestic gross against a $360,000 budget, transforming the cinema forever.

The movie wasn’t the only surprise smash—the soundtrack was one, too. Half a million records sold in the months after its release. Like everything else adjacent to Easy Rider, it was a fraught triumph. Supposedly, Fonda, as the film’s producer, had made a deal with the then ascendant Crosby, Stills & Nash to author the soundtrack. Again, it seems that Hopper was the impediment. He hated Fonda so much that he was hell-bent on destroying the collaboration with CSN. He supposedly rode in a limo with the band and said to them that “anybody who rides in a limo can’t comprehend my movie, so I’m gonna have to say no to this.” Then he threatened them with violence if they tried to get into the studio again. The deal fell through.

The compromise was an-on-the-fly amalgam of chart-toppers, deep cuts, and the sundry things the radio had on offer, chosen by Hopper based on what he was listening to while he was driving to work. There were licensing issues and genuine confusions—Hopper claimed this was the first time a soundtrack relied on existing music from popular artists of the day rather than songs specifically written and recorded for a project. There was little precedent for how to deal with securing the rights. The producers ultimately paid out $1,000,000 in fees, eclipsing the full budget of filming. And they more than got their money’s worth. After Steppenwolf’s opening barrage, a consistently moving and surprising bounty of radio hits from the era provides a ballast to the adventure and occasionally hints at the true conscience of the film. Ten songs over 38 minutes pregnant with danger and ecstasy, a mesmerizing, often-menacing guide for finding oneself by getting lost, or trying. It’s the sound of a light-hearted trip growing steadily heavier, until it’s too heavy to manage at all.

Thus, when it appears in Easy Rider, the Band’s exalted hippie-gospel “The Weight” feels entirely earned—it’s a handful of shaggy dog stories (with a literal shaggy dog in there), seeming to summarize the Quixotic nature of the flight to or from freedom both the filmmakers and film seemed to be tilting at. It is tempting at points to wonder if this was all a self-sabotage mission, and no one wanted the film to come out. Anyway, through some byzantine licensing fuck-up, they got to use the Band version in the picture, but not on the soundtrack. Still, they decided to include the song just the same, recorded by a Los Angeles band called Smith as a soundalike. It’s lovely, and somehow lonelier than the original, stripped of the Band’s all-for-one camaraderie and saddled with the strange off-brand feeling of an artisanal carbon copy.

When it segues into the Byrds’ “Wasn’t Born to Follow,” a lilting vision quest of a song written by Carole King and Gerry Goffin, the cumulative effect channels the mystic possibilities of the American open road, echoing Kerouac and Kesey, the dream logic progenitors of the ’60s counterculture. There is beauty in the chimerical imagery of the lyrics—sacred mountains, legendary fountains, leaves whose prisms of light form colors no one knows the name of—but also a profound melancholy. Writing about Woodstock, which took place the same summer as Easy Rider, Joni Mitchell would cast the generational wanderlust in liturgical terms: “We’ve got to get ourselves back to the garden.” Even in its many moments of national grandeur, Easy Rider and its soundtrack seem driven by an awareness that would later become the basis of a different Carole King classic: It’s too late.

This spirit of disillusion is shot through Jimi Hendrix’s colossal “If 6 Was 9,” a song which explicitly rejects orthodoxies of all kinds, from the condescending values of “white collar conservatives” to the peace-love wing of the counterculture. “If the sun refused to shine,” Hendrix snarls, “I don’t mind.” And then, as if to make himself explicitly clear: “If all the hippies cut off all their hair/I don’t care.” It’s a great song, but a frightening one as well, serving as a harbinger for the libertarian streak which would increasingly replace the foundational communal ethos of a rapidly fraying movement. Nature is turning nasty, chickens are coming home to roost, and terrible things are in the offing. None of this is Hendrix’s problem. “Fall mountains,” he sings, “Just don’t fall on me.”

One of the elements which makes Easy Rider such a strange and enduring experience is its curious admixture of the exhilarating, the dread-inducing, and the whimsical. Fraternity of Man’s “Don’t Bogart Me,” a sly stoner’s lament about missing out on the joint rotation, exudes the laid-back, offhand joy of an outlaw country novelty number, while the Holy Modal Rounders’ “If You Want to Be a Bird (Bird Song)” is simply silly—a hairbrained psychedelic waltz filled with admonitions to find heaven on earth by whatever means required. These are moments of release tinged with nostalgia for a simpler time slipping from view. Both songs are funny in a vacuum, but their juxtaposition with the darker elements of the film’s doom tour feels like the flickering embers of a dying dream.

Then there’s Roger McGuinn’s brilliant take on Bob Dylan’s formulative text “It’s Alright Ma (I’m Only Bleeding),” sped up subtly and somehow angrier than the original from 1965’s Bringing It All Back Home. A kind of national anthem of contrarianism, it’s a song which rejects established social hierarchies (“Even the president of the United States sometimes must have to stand naked”) and soulless consumerism (“Everything from toy guns that spark/To flesh-colored Christs that glow in the dark”) all while evincing a stringent self-reliance and skepticism about movementarian politics (“It is not he or she or them or it that you belong to”). McGuinn’s version is rueful and bitter, drenched in dashed hopes and disappointments. There is a sense that the song’s message had been misunderstood the first time—that it was not really about personal liberty, but rather personal responsibility. There is a feeling of wanting to go back and try again.

Easy Rider’s enigmatic gracenote comes just before the film’s apocalyptic ending, as Wyatt and Billy assess their journey over a campfire. Billy says, “We did it,” and he’s correct in the sense that they’ve gotten most of the way across the country with enough drug money to retire. Wyatt famously rejoins, “We blew it,” and everybody besides Billy knows it’s true. In a central irony, Easy Rider flexed the massive buying power of the ’60s counterculture just as the idealism that had been its north star "metastasized into paranoia and narcissism. The victory, if indeed that’s what it was, had proved a pyrrhic one. They were the epicenter of the culture, but the center wouldn’t hold. The rest of 1969 was filled with discouraging news. August would bring the Manson murders, perpetrated by a would-be guru who had smuggled his way into an L.A. music scene too stoned to notice the garden-variety psychopath in their midst. In December, the Stones’ free concert at Altamont would devolve into violence and chaos, as the Hells Angels, hired for security, started beating up the hippies. Easy Rider wants to know: Had they always been on the wrong road, or did they just make a wrong turn? The paradoxes kept piling up, the prison of freedom growing ever more impossible to escape.